I lost a bet to Jean (f/m,ff/m)

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Gil
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I lost a bet to Jean (f/m,ff/m)

Post by Gil »

Hello everyone 😊. It's been a long time since you've heard from me 😊. I apologize for this. I wasn't really motivated to write anything new because I had a lot going on in my personal life. I also didn't have many good ideas for new stories. Sure, you guys gave me a lot of ideas, even really good ones, but that also gave me motivation problems, like with the 400 Watcher special. I have to be 100% convinced of the topics etc. myself, otherwise, I find it difficult to write them. Unfortunately, that wasn't the case for me. I'll still keep the ideas in mind and you can still send me your ideas, but I want to write my topics first, or at least the topics, where I’m 100% convinced. I hope you understand and won't be too angry with me. Of course, I'm still trying to be as realistic as ever, but I'd like to bring some "fantasy" into my stories in the future, e.g. tape drones or haunted houses, etc. There are some very cool stories on these topics that I've read so far and I would like to incorporate them into future stories. I hope you continue to enjoy my stories. I'm now trying to write regular stories again, but I can't promise how regularly they will come. I hope I understand and forgive me 😊.
Your Gil 😊. Now, have fun with the story 😊:


Hello, it's Kyle again. This story happened the week after Lucas and I met my old babysitter, on Thursday. I was at school, hanging out with Jean at recess talking about this and that. Mostly about the next lesson. It was about math.

"I'm really curious about how last week's test turned out." She said to me.

"Oh yeah, me too. I'm curious to see which one of us got more points." I grinned at her.

"Definitely. Especially because of our little bet." She grinned. "You didn't forget about that one, did you?" She asked me.

"Of course, I didn't. Whoever gets more points on the test gets to order the loser anything they want until 9 pm after school today. So it's a little like the coupons I did, only modified." I explained again for understanding.

"Yeah, right. I'm getting excited." She grinned at me.

"Me too." I grinned back.

Then the bell rang for our next lesson and we went into the classroom. Our teacher didn't hand out the tests until the end. When I received my test, I looked at it immediately. 87/100 points.

"Yes, very good points. That will be hard for Jean to beat." I thought happily to myself.

I had already thought of something great to do. Clean my room, serve me, bondage could not be missing, of course, and so on. Then I looked at Jean and she at me. We sat down next to each other. I showed her my test and grinned. Then she started grinning and showed me hers. I couldn't believe it. 92/100 points. My ideas were just bubbling away. She grinned and I opened my mouth in amazement. She had won the bet. When the bell rang, she stood up and tapped me on the shoulder.

"Don't forget your TuG bag when you come to me. 4 pm." She whispered into my ear with a grin and left the classroom.

Somewhat dejectedly, I also got up and left the classroom. On the one hand, I was very happy about my achieved points, but on the other hand, I was not happy about the lost bet. When I got home, I grabbed my TuG bag, swung on my bike, and rode to Jean. I did most of my homework on the bus beforehand and the rest quickly at home. It wasn't much, thankfully. My parents already knew I was going to spend the day with her. During the ride, I wondered what she was going to do with me. When I arrived, her father opened the door for me and invited me in. I took off my shoes and walked up the stairs to Jean's room. I knocked and was invited in. She was sitting on her bed reading a magazine. She looked at me, grinned, and stood up.

"There's the loser." She grinned at me.

"Hey. At least I got a good grade on the test, too." I tried to tell myself.

"Yes, and that is good, but still lost." She grinned even more.

"...you're right." I said meekly and put the bag down.

"Good, you remembered." She said to me.

"Well sure, like I'd forget when it's needed." I grinned.

"Perfect." She winked at me. "But first, you need to get changed. Then I'll explain everything else.

"Okay, what should I wear?" I asked her, surprised because I had left all my costumes at home.

"This..." she said, opening her closet and handing me the clothes. "Well, do you recognize it?" She asked with a big grin on her face.

"...yes." I confirmed, slightly sobered. "The princess costume I wore to Spirit Week on gender swap day." I added.

"Yeah, you're right." She grinned at me. "So off to the bathroom to change. Because our bet has been on since you entered the house." She added.

"Do I have to?" I asked her.

She just looked at me and raised her eyebrows.

"Okay. A bet is a bet." I replied and walked into the nearby bathroom.

The costume looked like this, just for teenagers: https://images.halloweencostumes.com/pr ... incess.jpg
It was accompanied by pink ballerinas and the gloves were missing.

"Well, let me get this over with." I thought to myself and took off everything but my underpants.

I put on the dress, which still fit perfectly since I was very thin and Jean and I were almost the same size. Then I put on the ballerina shoes and put on the crown that was attached to a hairband. I looked at myself in the mirror and went straight to red in the face. I took my things and left the bathroom. When I arrived in Jean's room, she had already opened the TuG bag and was holding handcuffs, leg irons, and thumb cuffs. She looked over at me.

"Ohhhh, how cute." She grinned across both cheeks and looked at me.

"...thanks." I whispered to myself and put my clothes aside.

Then she came over to me and put the handcuffs around my hands, lifted the dress a little, and fastened the ankle cuffs around my ankles. She still left the thumb cuffs off.

"So my princess in distress. You don't look feminine enough yet. I'm going to change that." She said and took out her makeup utensils.

I snapped my eyes open. She put everything on her desk put a chair next to hers and tapped it a few times to signal me to sit down. I walked over to her and sat down in the chair. You could hear the footcuffs rustling very well. Then she started. She sat in front of me with red lipstick in her hand and started painting my lips. When she was done with that, she took eyeliner and went to work on my eyelashes. After that, I was supposed to close my eyes and she used pink eye shadow over my eyelashes. Finally, she painted my fingernails pink to match the costume. She took a few steps back and I just looked at her. She grinned broadly.

"Perfect. Your outfit is ready, Kylie." She grinned at me.

"Ohhh, please not the name." I asked her as I took my bound hands off the table, smirking slightly.

"Yes, it's just a perfect fit. And since I won, there's nothing you can do about it." She winked at me. "And if you get on my nerves too much, this will come into your mouth." She grinned, holding a ball gag in her hand.

"Okay, got it." I just nodded in acknowledgment.

"Let's get a nice picture for your boyfriend first then." She grinned and walked towards me.

She took a selfie of us. As I looked at the picture, it was easy to see how red my face was. I had no problem with her sending it to Lucas. He sent two smileys, wished us a good time, and that Jean should take care of his little princess. I was a little embarrassed about that. Luckily, it all stayed between us.

"So. Your first assignment is..." said Jean as she set the phone aside. "To do my homework." She grinned at me and picked up her bag.

"Really, your homework?" I asked her with a slight smirk.

"Sure. No one checks the handwriting. And I'm not up for it. So go ahead, Kylie." She grinned at me and handed them to me. I guess I had to put up with that name now.

"Handcuffed?" I asked her.

"Handcuffed." She answered bluntly.

So I set about doing her homework. Thank God I had done mine before and knew all the answers. It still took some time, because it was not easy to write well, quickly, and legibly with the handcuffs. From time to time I looked at Jean. She continued to read her magazine. The ball gag was next to her. I continued to do her homework. However, I was not a fan of this assignment.

"I thought you would come up with something better than doing your homework," I said to her.

She didn't answer, but I didn't turn to her either. Suddenly I saw a cloth in front of my eyes.

"Wait, wait, wait." Already she was stuffing a cloth into my mouth.

Before I could spit it out, she put the ball gag in my mouth and pushed it down my neck.

"I told you if you were too much of a pain, the ball gag would come into play." She grinned and I turned to face her. "HAHA, your lipstick is as red as the gag, haha." She laughed and sat back down on her bed.

I rolled my eyes and continued with their homework. It didn't take long for them to finish. I held them up.

"Doonmmhh." I said into my gag.

"Very good, Kylie." She said and came over to me.

She put her schoolwork aside and went back to thinking. I was curious about what she had in store for me next.

"Go downstairs and get two bottles of water." She said to me.

"Downstairs?" I thought and jerked my eyes open questioningly.

"Yes. My parents are gone until tonight anyway and the only one who could see you would be my sister." She said.

"That doesn't make it any better though." I thought to myself and headed out.

I heard the handcuffs, but I made it down the stairs to the kitchen without running into Susan (Jean's little sister). I grabbed two water bottles from the fridge and quickly headed back upstairs. I made it without Susan seeing me. I was very relieved.

"Ah, perfect." she said, coming up to me and taking the two water bottles.

She took a sip and I just looked at her. I was thirsty, too.

"Do you want something to drink? She asked me.

"Meeeppphh." I nodded.

"Then hold out your hands." She prompted me.

I did as she asked, and suddenly I noticed her putting the thumb cuffs around my thumbs. I just looked at her dully.

"What, it's much more fun this way." She grinned widely.

"Yeah, for you anyway." I thought to myself.

"So. First the next task, then you get something to drink." She said. I was curious to see what came next. "You're going to clean my room and tidy it up. The things to clean are in the broom closet at the end of the hall." She said to me.

"Haha, that's what I thought if I had won." I thought to myself and had to smile slightly inside.

I nodded in affirmation, since I had no choice but to follow her anyway, and went back down the stairs. Once in the broom closet, I grabbed a bucket, rag, detergent, hand brush, and dustpan and quickly went back to Jean's room. Once there, I put everything down and began to clean up. Jean was watching TV in the meantime. I cleaned dirty clothes off the floor onto a pile, cleaned her desk, made her bed, etc. As best I could, with my hands and thumbs tied. It wasn't easy, especially making the bed. Then I gave everything a good wipe-down. I swept up a little dirt with the hand brush and tried to do it on the dustpan. It wasn't easy.

"The stupid thumb cuffs." I thought to myself.

It would be much easier without them, but that was Jean's intention, that's why she had put them on me. After a long while, I was ready.

"Weadyy." said I, putting everything aside.

"Very well done Kylie." She said and looked around carefully. "Now you can get something to drink." She added with a grin.

She walked over to me, undid the ball gag, and took it out of my mouth. I spit the material out. Jean held the open water bottle out to me, took it, and drank a large amount of it.

"Whew, finally." I said to her as I gulped it down.

"Haha, you did good Kylie." She said to me with a grin.

"Thanks. I think a maid costume would have been more appropriate today." I said to her.

"Haha, yes that's true, but I don't have one. But maybe in the future." She laughed.

I laughed too and then looked at the clock. It was already 7 pm. Two more hours and I would be free.

"I can't think of any more tasks either." said Jean to me while she was still thinking.

"And now that you can't think of anything?" I asked her.

"Then I'll just tie you up for the rest of the time." She grinned.

"Okay, I'll be happy with that.” I grinned back.

"Well then, open your mouth." She said, holding the cloth and ball gag in her hand.

I did as she told me. She put the cloth back in my mouth and also the ball gag, which she locked around my neck. Then she loosened the thumb, hand, and foot cuffs. So now I was only gagged. Then she took various ropes from my TuG bag and also duct tape.

"Stretch out your arms and make fists. ", she asked me, which I did immediately.

She wrapped my hands with tape. So I had, as so often, 2 small silver balls instead of hands. So any attempt to escape was pointless. Then she took a 5-yard rope, led my arms backward, and tied them crosswise together. She still placed the knot over my hands, as if that would make a difference. Then she took a long 25-yard rope and tied it to my hands. Then she began to wrap it around my torso, all the way up to my shoulders. Now and then she knotted it tightly to keep it in place. My upper body was already tied up very well. Then she took 3 ropes again, each 5 yards long. The first rope she tied above my knees. To tie it, she had to lift the dress and had some difficulty tying it. I had to smile slightly at that. Then she did the same below my knees and around my ankles. Then she carefully laid me on the floor and got another 5 yards of rope. She wrapped it halfway around my ankles, then angled my legs and tied the rest tightly around my wrists. So a classic hogtie that was pretty tight. Then she took off my shoes and socks and tied my toes together with a small cable tie.

"You know what's coming now, don't you?" she asked as she sat down at my feet.

I nodded in agreement. I knew she was going to tickle me, as she often did.

"Right. It's tickle time." She grinned and started already.

"MAMAMAHAMAHHAM MHAHHMAHHAMHA MHAHAMHMAHMHAA MHAMAHMAHMA." I laughed into my gag.

I wriggled back and forth but didn't have much room to move. Even the cable tie around my toes was helping Jean tickle me more easily. Her nails weren't helping either. They were quite long and so could be even more annoying. She tickled me incessantly. I laughed very loudly, despite my gag, until the door opened.

"What's going on here?" I heard a voice ask. It was Susan, Jean's little sister.

I turned to her and immediately blushed. Now she saw me like that, which I didn't want at first.

"Ah, I see. So you won the bet, sis. Congratulations." Grinned she over to us. "You look very handsome, by the way, Kyle." Grinned she at me.

"Wait. Did Jean tell Susan about our bet? Great, so she knew all along." thought I to myself.

"Thanks, Susan. Want to help tickle him?" She asked Susan.

"Sure, I wouldn't miss it." She grinned and joined in.

Then Jean started again and Susan started tickling and poking my sides. This was bad for me because I was so ticklish. Both of them showed no mercy. From time to time they both laughed and were having fun. From time to time they exchanged positions. That was then times the only short time where I could breathe. I often had to laugh so hard that I started to cry. At about 8 pm they finally let go of me, after about 1 hour of continuous tickling.

"Come on, let's let Kylie take a breath for the last half hour and leave her alone." suggested Jean, which Susan confirmed.

I just lay there and calmed down from all the tickling. Breathed deeply. The two of them chatted about what I had to do, etc. They both had to laugh. I was a little embarrassed, but also found it a little funny. At least this way I could still enjoy the bondage a bit without getting annoyed. The hogtie was pretty tight, but not painful, at least for the duration so far. At 8:30 pm, however, the two of them came back to me and I suspected bad things.

"Don't worry, you won't be tickled." Said Jean, which made me breathe a little easier. "We'll let you out now so you have plenty of time to change, take off your makeup, etc." she added, already starting to undo the hogtie.

"Mmmeeepphh." I nodded in agreement.

Susan, meanwhile, was freeing my hands from the tape. When they were both finished, they straightened me out. Susan then freed my upper body from the long rope and Jean started on my legs. When my upper body was free, all that was missing were my hands and my knees. Shortly after I was also free and stretched briefly, I looked at them both and they laughed. The makeup was blurred by crying. I then grabbed my stuff, and makeup remover from Jean and went into the bathroom. I took off my makeup, then took off my dress and the crown. I put my normal clothes back on and went back to Jean's room. They had already cleaned up all the ropes, etc and put them in my TuG bag. Everything was clean and tidy.

"Ah, there's Kyle again and not Kylie anymore." Grinned Susan at me.

"Haha, very funny," I grinned back and passed the costume to Jean.

"Oh come on. It was funny." She said to me.

“Yes, definitely more for you this time than for me. But that was the point of the bet." I replied.

“Yes, you’re right.” She grinned at me and hugged me.

It was now shortly before 9, I packed up my things, said goodbye to Jean, Susan, and their parents, who were also at home by now, and headed home.


The End


I hope you like my story 😊

If you have an idea for a scenario or costume, just post it in the comments or private message me, and I’ll try to incorporate it into the stories as best I can and I will link you. Thank you 😊.

My DeviantArt Account: https://www.deviantart.com/gil115
My TuGstories Account: https://tugstories.com/memberlist.php?m ... file&u=272
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Stormee
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Post by Stormee »

Hey @Gil!

Great to see you writing again. Always fun to see Kyle and Jean at it again with their fun games and trying to see who will tie up the other through bets or anything. I did see your post on Deviantart on how you want to do more fantasy writing with Kyle with the tape bots or anything. That would be cool to read. Anyway, great story again to continue the adventures of Kyle. :D
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Gil
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Post by Gil »

Stormee wrote: 2 months ago Hey @Gil!

Great to see you writing again. Always fun to see Kyle and Jean at it again with their fun games and trying to see who will tie up the other through bets or anything. I did see your post on Deviantart on how you want to do more fantasy writing with Kyle with the tape bots or anything. That would be cool to read. Anyway, great story again to continue the adventures of Kyle. :D
Hello @Stormee

Thanks a lot :)
I will try to make it more regular again now. I won't promise a specific time period, but I'll try to make it relatively regular again.
Yeah, let's see what else I can think of :D how to incorporate it well.
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Post by Red86 »

Indeed @Gil, long time no see. Sorry I missed this. Always fun to see what shenanigans Kyle and his tug group end up getting into!
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Madame_du_Barry
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Post by Madame_du_Barry »

Love it! Please continue :)
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Gil
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Post by Gil »

@Red86 @Madame_du_Barry , glad you liked it and thanks for your comments :D
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Post by Oyster stew 2.0 »

Story idea:make it so now Jean is either stronger or knows some martial arts and forcefully hogties him to get him to stop annoying her
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